Modular continuous flow synthesis of imatinib and analogues
A modular continuous flow synthesis of imatinib and analogues is reported. Structurally diverse imatinib analogues are rapidly generated using three readily available building blocks via a flow hydration/chemoselective C-N coupling sequence. The newly developed continuous flow hydration and amidatio...
| Main Authors: | , |
|---|---|
| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
American Chemical Society (ACS)
2020
|
| Online Access: | https://hdl.handle.net/1721.1/125954 |
| _version_ | 1826196411405828096 |
|---|---|
| author | Fu, Wai Chung Jamison, Timothy F |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Fu, Wai Chung Jamison, Timothy F |
| author_sort | Fu, Wai Chung |
| collection | MIT |
| description | A modular continuous flow synthesis of imatinib and analogues is reported. Structurally diverse imatinib analogues are rapidly generated using three readily available building blocks via a flow hydration/chemoselective C-N coupling sequence. The newly developed continuous flow hydration and amidation modules each exhibit a broad scope with good to excellent yields. Overall, the method described does not require solvent switches, in-line purifications, or packed-bed apparatuses due to the judicious manipulation of flow setups and solvent mixtures. |
| first_indexed | 2024-09-23T10:26:25Z |
| format | Article |
| id | mit-1721.1/125954 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T10:26:25Z |
| publishDate | 2020 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1259542022-09-30T21:09:32Z Modular continuous flow synthesis of imatinib and analogues Fu, Wai Chung Jamison, Timothy F Massachusetts Institute of Technology. Department of Chemistry A modular continuous flow synthesis of imatinib and analogues is reported. Structurally diverse imatinib analogues are rapidly generated using three readily available building blocks via a flow hydration/chemoselective C-N coupling sequence. The newly developed continuous flow hydration and amidation modules each exhibit a broad scope with good to excellent yields. Overall, the method described does not require solvent switches, in-line purifications, or packed-bed apparatuses due to the judicious manipulation of flow setups and solvent mixtures. DARPA (contract no. ARO W911NF-16-2-0023) 2020-06-23T19:37:48Z 2020-06-23T19:37:48Z 2019-07 2019-12-18T17:55:25Z Article http://purl.org/eprint/type/JournalArticle 1523-7052 https://hdl.handle.net/1721.1/125954 Fu, Wai Chung, and Timothy F. Jamison, "Modular continuous flow synthesis of imatinib and analogues." Organic Letters 21, 15 (July 2019): p. 6112-16 doi 10.1021/ACS.ORGLETT.9B02259 ©2019 Author(s) en 10.1021/ACS.ORGLETT.9B02259 Organic Letters Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) Other repository |
| spellingShingle | Fu, Wai Chung Jamison, Timothy F Modular continuous flow synthesis of imatinib and analogues |
| title | Modular continuous flow synthesis of imatinib and analogues |
| title_full | Modular continuous flow synthesis of imatinib and analogues |
| title_fullStr | Modular continuous flow synthesis of imatinib and analogues |
| title_full_unstemmed | Modular continuous flow synthesis of imatinib and analogues |
| title_short | Modular continuous flow synthesis of imatinib and analogues |
| title_sort | modular continuous flow synthesis of imatinib and analogues |
| url | https://hdl.handle.net/1721.1/125954 |
| work_keys_str_mv | AT fuwaichung modularcontinuousflowsynthesisofimatinibandanalogues AT jamisontimothyf modularcontinuousflowsynthesisofimatinibandanalogues |